N-(2,2-diethoxyethyl)-N'-(2,4-difluorophenyl)urea → 1-(2,4-difluorophenyl)-2(1H,3H)-imidazolone

HRID 1077893Notes

Reaction equation

HRID 1077893 reaction equation
C(O[CH:4](OCC)[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17])=[O:8])C>CO.O.Cl>[F:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[N:9]1[CH:4]=[CH:5][NH:6][C:7]1=[O:8]

Participants

5

Reactant 1

HCID 19065111N-(2,2-diethoxyethyl)-N'-(2,4-difluorophenyl)urea

Product 1

HCID 190650921-(2,4-difluorophenyl)-2(1H,3H)-imidazoloneYield 89.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

This urea compound (37.5 g) was dissolved in a mixture of 560 ml of methanol and 280 ml of water, 300 ml of 0.48M hydrochloric acid was added thereto and the mixture was stirred at room temperature for three days. The reaction solution was concentrated under reduced pressure and the crystals separated out were washed with a mixture of water and methanol (5:1) to give 22.8 g of 1-(2,4-difluorophenyl)-2-(1H,3H)-imidazolone as a colorless powder.

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe crystals separated out
  4. washwere washed with a mixture of water and methanol (5:1)

Sources & evidence

ORD record
ord-fd1afeae18914c18ad6669ea4a3ee72f
Source dataset
uspto-grants-1996_08
Patent number
US05545652

Reaction notes

Loading…